Acetone → 1-{[1-(2,4-Dichlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-one

HRID 969222Notes

Reaction equation

HRID 969222 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12]([N:14]2[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15]2)=[O:13])[CH2:11][CH2:10]1.CC(C)=O>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12]([N:14]2[CH2:18][CH2:17][C:16](=[O:19])[CH2:15]2)=[O:13])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 180AcetoneHCID 666627281-{[1-(2,4-Dichlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-ol

Product 1

HCID 666624751-{[1-(2,4-Dichlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solutin of 1-{[1-(2,4-dichlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-ol (3.05 g, 0.0102 mol) in acetone (50 mL, 0.7 mol) was added Jone's oxidant in water (8.00 M, 2.54 mL) at 0 degrees celsius and the resulting solution was stirred at rt for 1 hour. The mixture was filetered through celite and the filtrate was concentrated. The resulting residue was dissolved in AcOEt, washed with water and brine successively, dried with MgSO4, and concentrated in-vauo. The crude product was purified by Combiflash eluting with 40% AcOEt in hexanes.

Workup

  1. concentrationthe filtrate was concentrated
  2. dissolutionThe resulting residue was dissolved in AcOEt
  3. washwashed with water and brine successively
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in-vauo
  6. customThe crude product was purified by Combiflash
  7. washeluting with 40% AcOEt in hexanes

Sources & evidence

ORD record
ord-5713709cdc2246c2a8dbf12819c8aa96
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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